1-Octene → HCID 53759644, compound

HRID 54872Notes

Reaction equation

HRID 54872 reaction equation
[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Br[C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:20][C@@H:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[O:18][C:17]2=[O:27])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.CN(C=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:20][C@@H:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[O:18][C:17]2=[O:27])=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

7

Reactant 3

HCID 81251-OcteneHCID 11430Potassium CarbonateHCID 54447613HCID 54447613, compound

Product 1

HCID 53759644HCID 53759644, compoundYield 17%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

0.40 g (3.56 mM) of 1-octene and 2 ml of dry tetrahydrofuran (THF) were placed in 50 ml-three necked flask. To the mixture, 7.6 ml of 0.5M-9-borabicyclo[3.3.1]-nonane-(9-BBN) in THF was gradually added dropwise on an ice-common salt bath at -15° to -13° C. (inner temperature) in nitrogen atmosphere, followed by stirring for 1 hour at the same temperature and further stirring for 2 hours at about 10° C. To the resultant mixture, a solution of 0.80 g (2.51 mM) of (5R)-3-(4-bromophenyl)-5-phenyl-2-oxazolidinone synthesized in Example 3 in 11 ml of DMF was added under cooling on an ice bath, followed by addition of 0.08 g of tetrakis (triphenylphosphine) palladium (O) and 0.70 g of potassium carbonate in succession and then stirring for 3 hours at 63.5°-70 ° C. (inner temperature). After the reaction, the reaction mixture was poured into ice water to precipitate a crystal. The crystal was recovered by filtration and washed with water, followed by purification by silica gel column chromatography (eluent: hexane/ethyl acetate=4/1) and recrystallization from acetone to obtain 0.15 g of (5R)-3-(4-octylphenyl)-5-phenyl-2-oxazolidinone (Yield: 17.0%).

Workup

  1. stirringfurther stirring for 2 hours at about 10° C
  2. temperatureunder cooling on an ice bath
  3. stirringstirring for 3 hours at 63.5°-70 ° C. (inner temperature)
  4. customAfter the reaction
  5. customto precipitate a crystal
  6. filtrationThe crystal was recovered by filtration
  7. washwashed with water
  8. customfollowed by purification by silica gel column chromatography (eluent: hexane/ethyl acetate=4/1) and recrystallization from acetone

Sources & evidence

ORD record
ord-f2814c9c67c34898914919edca5aa9c6
Source dataset
uspto-grants-1997_04
Patent number
US05624600

Reaction notes

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